Potassium Carbonate → Ethyl 1-benzyl-4-(4-methoxyphenyl)sulfonylpiperidine-4-carboxylate

Participants

Reaction Steps

To a stirred solution of bis-(2-chloro-ethyl)-benzyl amine hydrochloride (6.6 g, 24.7 mmol), 18-Crown-6 (500 mg), and anhydrous K2CO3 (30 gmn, excess) in dry acetone (250 ml), (4-methoxy-phenylsulfonyl)-acetic acid ethyl ester (6.12 gm, 24 mmol) was added in a round bottom flask and the reaction mixture was heated at reflux for 16 hours with good stirig. At the end, the reaction miixture was allowed to cool and the potassium salts were filtered off and the reaction mixture was concentrated. The residue was extracted with chloroform and washed with H2O. The organic layer was furher washed well with water, dried over MgSO4, fitered and concentrated. The dark brown reaction mixture was purified by silica gel couinn chromatography by eluting it with 30% ethylace tate: hexane and the product 4-(4-Methoxy-benzenesulfonyl)-1-benzyl-piperidine-4-carboxylic acid ethyl ester was isolated as Brown oil. Yield: 6.0 g, 60%; MS: 418 (M+H).

Provenance & Evidence